1547-15-5

Basic information

• Product Name: 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE
• Synonyms: 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE;3-(4-FLUOROPHENYL)-2-THIOXO-2,3-DIHYDRO-4(1H)-QUINAZOLINONE;2,3-Dihydro-3-(4-fluorophenyl)-2-thioxo-1H-quinazolin-4-one;2,3-Dihydro-3-(4-fluorophenyl)-2-thioxoquinazolin-4(1H)-one;3-(4-Fluorophenyl)-4-oxo-1,2,3,4-tetrahydro-2-thioxoquinazoline;3-(4-fluorophenyl)-2-sulfanylidene-1H-quinazolin-4-one;3-(4-fluorophenyl)-2-thioxo-1H-quinazolin-4-one;JS-208C
• CAS NO: 1547-15-5
• Molecular Formula: C₁₄H₉FN₂OS
• Molecular Weight: 272.3
• Mol File: 1547-15-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: >250
• Boiling Point: 430.1 °C at 760 mmHg
• Flash Point: 213.9 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Refractive Index: 1.725
• CAS DataBase Reference: 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE(1547-15-5)
• EPA Substance Registry System: 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE(1547-15-5)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 1547-15-5(Hazardous Substances Data)

Usage

General Description

3-(4-Fluoro-phenyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one is a chemical compound with potential pharmaceutical applications. It belongs to the quinazolinone family and is characterized by a thioxo group and a 4-fluoro-phenyl substitution. 3-(4-FLUORO-PHENYL)-2-THIOXO-2,3-DIHYDRO-1H-QUINAZOLIN-4-ONE may exhibit biological activities such as anti-inflammatory, analgesic, anticonvulsant, and anticancer properties. Its structural features make it a promising candidate for drug development, particularly in the treatment of various diseases and conditions. Further research and studies are needed to fully understand the potential benefits and risks associated with this chemical.

InChI:InChI=1/C14H9FN2OS/c15-9-5-7-10(8-6-9)17-13(18)11-3-1-2-4-12(11)16-14(17)19/h1-8H,(H,16,19)

Upstream product

• 118-92-3 anthranilic acid 
• 1544-68-9 4-fluorophenyl isothiocyanate 
• 75-15-0 carbon disulfide 
• 216502-06-6 2-amino-N-(4'-fluorophenyl)benzamide 
• 118-48-9 isatoic anhydride 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 33692-68-1 N-(4-fluorophenyl)methyl dithiocarbamic acid 
• 371-40-4 4-fluoroaniline 
• 134-20-3 2-carbomethoxyaniline 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 16024-82-1 methyl 2-isothiocyanatobenzoate 
• 19182-34-4 ammonium p-fluorophenyldithiocarbamate 
• 16332-89-1 3-(4-Fluorophenyl)quinazoline-2,4(1H,3H)-dione 

Downstream Products

• 1298113-86-6 C₁₆H₉FN₄O₃ 
• 1017084-43-3 C₂₃H₁₇FN₂O₂S 
• 443347-74-8 C₂₂H₁₄ClFN₂O₂S 
• 67811-51-2 4-(4-fluorophenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one 
• 66679-71-8 2-hydrazino-3-(4-fluorophenyl)quinazolin-4(3H)-one 

Relevant articles and documents

Design, synthesis, and anti-inflammatory activity of novel quinazolines

Several new fluorinated quinazolinone derivatives were prepared and evaluated for in vitro anti-inflammatory activity. The molecular modelling study was performed for compounds 4, 8, 9, 10 and 13. The tested compounds showed strong interactions at the COX

Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives

A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.

CuBr-catalysed one-pot multicomponent synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives

A novel methodology is presented for the synthesis of 3-substituted 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives based on an efficient tandem multicomponent reaction using copper bromide as catalyst. This methodology is based on the multicomponent one-pot reaction of methyl 2-bromobenzoate, phenylisothiocyanate derivatives and sodium azide in the presence of copper bromide and l-proline under basic conditions. To show the generality of the method, various phenylisothiocyanates bearing electron-donating or electron-withdrawing functionalities were used and the desired products were obtained in high isolated yields.